CA2448618A1 - New 2,2'-azino-bis-thiazolines as precursors to air-stable radicals - Google Patents

New 2,2'-azino-bis-thiazolines as precursors to air-stable radicals Download PDF

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CA2448618A1
CA2448618A1 CA 2448618 CA2448618A CA2448618A1 CA 2448618 A1 CA2448618 A1 CA 2448618A1 CA 2448618 CA2448618 CA 2448618 CA 2448618 A CA2448618 A CA 2448618A CA 2448618 A1 CA2448618 A1 CA 2448618A1
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alkyl
chc
c6h4c
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Amer Hammami
Michel Armand
Hicham Cavalie
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Priority to PCT/FR2004/002320 priority patent/WO2005026136A2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/18—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

NEW 2,2'-AZINO-BIS-THIAZOLINES
AS PRECURSORS TO AIR-STABLE RADICALS
Invention by Michel Armand, Amer Hammami, Hicham Cavalie, What we claim is:
1 ) New compounds of the general formula:
R
where:
RF is an organic halogenated organic radical, alkyl, aryl, aryl-alkyl, alkyl-aryl, heterocyclic, alkyl-heterocyclic, heterocyclic-alkyl-, in which at least than 40% of the hydrogen atoms are replaced by either chlorine or fluorine, possibly including catenary heteroatoms in the for of -O-, =N-, -S-, =P-, =(P=O) -, -SO-, -SOz- from 1 to 28 carbon atoms, or is part of a polymer chain or network.
R is an organic radical from 1 to 400 carbon atoms, or is part of a polymer chain or network.
R' isHorR
2) Compound according to claim 1 characterised in that RF is F, Cl, CF3, C"Fz"+i, HC"Fzn+i-, CF30-, C~Fz~+~O-, HC"Fz~+lO-, CF3S-, CnFzn+iS-, HC"Fzn+tS-,C1C"Fz"~-i-, C1C"Fzn+~O-, CICnFz~+iS-, BrC"Fzn+~-, BrC"Fz~+i0-, BrC"Fz"+i S-, I CnFz"+1-, I C~F2n+i O-, I C"FZn+~ S-, C Hz=CHC"Fz"+i-, CHz=CHCnFzn+10-~ CHz=CHCnFzn+1S-, RzOCnFzn+1-, RzOCnFzn+10-, RZOCnFzn+~S-, CF3CHz-, CF3CHz0-, (CF3)2CH-, (CF3)zCHO-, CHF2-, CHFzO-, CHFZS-, CCIFz-, CC1F20-, CC1FZS-, , CCIzF-, CClzFO-, CC1FZS-, CC13,-CC13O-, C6F5-, CF3C6F4-, C6FSO-, CF3C6F4O-, 3,S-(CF3)zC6H2-, C6C15-, C6C150-, FSOZCFz-, CISOz(CFz)ri , -S03(CFz)~ , -S03(CFz)~ , 'COz(CFz)ri , -S03(CFz)ri , 'z03P(CFz)n , FSO2N~-~SOz(CFz)n , CF3SOZN~-~SOz(CFz)n , C~Fz"+1SOZN~-~SOz(CFz)"-, R'SOZN~-~SOz(CFz)n , FSOz(CFz)~ , CISOz(CFz)ri , -S03(CFz)n-, 'S03(CFz)ri , ~COz(CFz)p , -S03(CFz)~ , CnFz~+~ S02N~ ~(CFz)n , R' S02N~~?(CFz)~ where Rz has a similar definition than R, and 2 < n < 12.
., ., RF' RF
3) Compound according to claim 1 characterised in that R is an alkyl, alkenyl, an aryl-alkyl, an aryl-alkenyl, an alkyl-aryl, an aryl-alkenyl, an alkyl-heterocyclic, heterocyclic-alkyl, from 1 to 28 carbon atoms, possibly including catenary heteroatoms in the for of -O-, =N-, -S-, =P-, =(P=O)-, -SO-, -SOZ- possibly bearing various functionalities 4) Compound according to claim 3 characterised in that the various functionalities include negative or positive ion-bearing groups, hydroxy, amine, solvating or complexing capabilities, double bonds and polymerization-active functionalities.
5) Compound according to claim 3 characterized in that R is chosen from CpHZp+1-, C6H5-, C6HSCpHZp , CpH2p+IC6H4-~ CpHzp+IC6HaCrH2T ~ CHz=CHCpHzp , CH2=CHC6H5-, CH2=CHC6H4CpH2p+1-, CHZ=CHCPHZpC6H4-, O CpH~,- , HOCpHZp , (HO)CHZCH(OH)CpH2p , HO[CZH40]aCrHZ~ , CpHZp+10 U2H40~qCrH2r (HO)CHZCZH40CzH4-, HOC6H5-, HOCHZC6H5-, HOCpH2p+IC6Ha-, HOC6HaCPH2p+1-, HO CpH2pC~H4 CPHZp , CH2=CHC(=O)OCPHZp , CH2=CHC(=O)OC6H4-, CHZ=CHC(=O)OC6H4-, CH2=CHC(=O)OCpH2pC6H4-, CHZ=CHC(=O)OCpH2pC6Hy CrH2t-, CHZ=C(CH3)C(=O)OCPHZP , CHz=C(CH3)C(=O)OC6H4-, CHZ=C(CH3)C(=O)OCpH2pC6H4-, CHZ=C(CH3)C(=O)OCpH2pC6H4CrH2r-, OZCCpHZp , 02CC6Hq-, [ 02C~2C6I"13-~ L 02C~3C~H3m OzC CpH2pC6H4-OZCCpHZpC6H4CrH2,.-, 03SCpH2p , 03S C6H4-, [ O3S]ZC6H3-, C 03S]3C6H3-, 03SCpHZpC(Hq-s 03.5 CpH2pC6H4CrH2t ~ 203PCpH2p , 203PC(H4-, [ 203P]ZC6H3-, [ 203P]3C6H3-, z03PCpH2pC(,H4-, ZO3PCPHZpC6H4CrH2r, CF3SOZN~ ~OZSCpHZp , CF3SOZN~ ~OZSC6H4-, [CF3SO2N~ ~OZSJ2C6H3-, jCF3SOzN~ ~OZS]3C6H3-, CF3SOzN~ ~OzSCpH2pC6H4-, CF3SOZNt ~OZSCpHZpC6H4C,H2r-, N~CNt ~OZSCpHzp , N-CND ~OZSC6H4-, [N---CN( )OZS]zC6H3-, [N~CN~ >Nc ~OZS]3C6H3-, N~CNt ~OZSCpH2pC6Hd-, N---CND ~OZSCpH2pC6H4CrHz~ , (N=C)ZC( )OZSCpHzP , (N-C)ZC( )OZSC6H4-, L(N$C)aC~ ~OZS~2C6H3-, ~(N$C)2Cc >Nc >OZS~3C6H3-s (N~C)ZC~-~N~-~OZSCpH2pC6H4-, (N=C)ZC~-?N~'~OZSCpH2pC6H4C~Hz,~, [CSHzs+1]3t+~NCpHZP ~ UCSHzs+a3~+~NC6H4-,[CSHzs+1]3~+~NC6H3-, ~~CsH2s+1~3~+~N~3C6H3-~ ~CsH2s+1~3~+~CpH2pC6H4-, ~CsH2s+1~3~+~CpH2pC6HqCrH2r--~ ~CsH2s+1~3~+~NCpH2p , (~CsH2s+1~3~+~PC6H4-,~CsH2s+1~3~+~PC6H3-, ~~CsH2s+1~3~+~P~3C6H3-~
~CsH2s+1~3~+~PCPHZPC6H4 > ~CsH2s+1~3~+~PCPHZpC6H4CrH2W~
(LCSH2S+n2~+~SC6H4-,[CSHZs+y2~+~SCsH3-, ~LCsH2s+1]2~+~s}sC6H3-~CsH2s+1~2~+~SCPHZPC6H4 s ~CsH2s+1]a~+~SCpHzpCsHaCrH2a~ CsH2s+n+~LNCaHa]-CsH2s+1~+~LNC3H3N~CPH2P ~ ~CsH2s+lOJ3s1 CpHZp-~ ~CsH2s+10~251(CH3) CpH2p-Where: ( 1 < n, p < 48), (0 < s < 18) 6) Compound according to claim 1 characterised in that is formed form two moieties A-B, either A or B, alternatively A and B being chosen from:

H3 ~ H3 ~ H3 N N N
N= ~N t--N
F3C ~ S C2F5 _' S CeFs ' ~S
12H5 l2Hs 12H5 N N N
~N N- N
F3C ~S/ C2Fs 1S C4F9 ~S

N N N
N N= N
F3C ~ S C2Fs _ S C4F9 ~ S
sHl3 ~ sHl3 ~ sHl3 N N N
N N ~N
F C 'S C F \ S C4F9 ~ ~S
8H17 ~ 8H17 ~ 8H17 N N N
N ~N r--N
C ~S CzFs "S C4F9 "S
C12H2s 1 lzH2s 1 l2Hzs IIIN N N
N N~ N
~ S C2F5 -. S CaFs w S

16H33 ~ 16H33 ~ 12H25 N N N
N ~N- ~N
F3C ~g C2Fs ~S C4F9 'S

IN N N
---N J--N t--N
F3C ~S~ C2Fs "S C4F9 "S

N
~N
F3C ' S C2Fs CaFs IHs IH3 N N
J--N- r---N
H3C0--C 'S HgCS-C ~S
Fp F2 I Hs ( Hs N N
r--N= 1--N=
C2Hs0-F ~S~ C2HsS- z ~ ~S

I H3 ~ H3 N N
N J---N
~S
H3C0-(C2H40)n-F2 S H3C0-(CZH4S)n-F

N N
----N ~N
OOC-(H2C)p-O--F S OOC-(H2C)p-S- z S

N N
r--N- J--N
OaS -(HzC)P - O - C S OsS-(HzC)P - S- C ~ ~S

N
02S-N-S02 j--N
I F3 IH2C)P-S-F ~S
z N

F3 ~H2C)P-O-C S

I H3 CHs N
N- O N
_ H2 _ S

Hs CH3 N
~N- N
H H S
Br-C \S HO-C? C? O-C

N N
t--N O r--N
II H2 H ~2 F2HC S H2C=H-C-O-C-C-O-F S

N
j-N= CHg O N
H
HF2C-C S H2C= ~ -II-O-Cp C? O-C S

N
t--N
H_ _ ~S

Hp O
H2 ~ -C-OH (CH2)P-CH \CH2 N
N
N ~
r--N-F3C S FsC ~S

H2C-C? (O-C? CHz)n-OCHa (CHz)p-N=C=O
N
N ~N
S
F3C ~ S F3C
(CHz)PrC00 ICHz)P-O II H CHz N O
N- ~N
~S
FaC S F3C
(GHz)P-SOa (CHz)P-O-C-C-CHz Ha N
N- ~N
F C S FaG ~ S

_ CHa IGHz)P-SOz-N-SOz-CFa (GHz)P-N~

N N
~N- N
FsG ~ S FaC w S
+/CHa (CHz)P-CH=CHz ICHz)P-N,\CHa \\ N
N CHa S N
~ S F3C

N
J--N
FaC ,S

~N
N
N ~
J-- N =
~N

N/
N
~N
F C ' F3C 'S
7) Polymer or co-polymers characterised in that they are prepared from the polymerisation or copylmerisation of compounds according to claim 1 containing active functionalities in R, R' of RF
8) Polymers or co-polymers characterised in that it comprises the repeat units:
~nr"
n where Q is a divalent organic radical containing between 1 and 240 carbon atoms and possibly including catenary heteroatoms in the for of -O-, =N-, -S-, =P-, =(P=O) -, -SO-, -SOZ-9) Polymer or co-polymers characterised in that it comprises the repeat units:

R~ N S RF
~N-N I
S
3P ~ R
R
where vw~n, represents a divalent organic radical containing between 1 and 240 carbon atoms and possibly including catenary heteroatoms in the for of -O-, =N-, -S-, =P-, =(P=O) -, -SO-, -SOZ-.
10) Compounds according to claim 1 to 9 characterised in that the azino-bis-thiazoline units can form a radical cation and possibly a radical di-cation.
11) Compounds according to claim 10 characterised in that the radical canon is stable to air and to water.
12) Compound according to claim 1, as discrete molecule or under polymeric form characterised in that it is used as a redox mediator.
13) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used as an assay for laccases.
14) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used as redox shuttle for lithium batteries, either with liquid electrolytes or with polymeric electrolytes.
15) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used as active component for electrochromic windows.
16) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used a mediator for redox fuel cells on the positive electrode side.
17) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used a mediator for bleaching paper pulp and fibers with oxygen.
R

Claims (17)

1) New compounds of the general formula:
where:
R F is an organic halogenated organic radical, alkyl, aryl, aryl-alkyl, alkyl-aryl, heterocyclic, alkyl-heterocyclic, heterocyclic-alkyl-, in which at least than 40% of the hydrogen atoms are replaced by either chlorine or fluorine, possibly including catenary heteroatoms in the for of -O-, =N-, -S-, =P-, =(P=O) -, -SO-, -SO2- from 1 to 28 carbon atoms, or is part of a polymer chain or network.
R is an organic radical from 1 to 400 carbon atoms, or is part of a polymer chain or network.
R1 is H or R
2) Compound according to claim 1 characterised in that R F is F, Cl, CF3, C n F2n+1, HC n F2n+1-, CF3O-, C n F2n+1O-, HC n F2n+1O-, CF3S-, C n F2n+1S-, HC n F2n+1S-, ClC n F2n+1-, ClC n F2n+1O-, ClC n F2n+1S-, BrC n F2n+1-, BrC n F2n+1O-, BrC n F2n+1S-, IC n F2n+1-, IC n F2n+1O-, IC n F2n+1S-, CH2=CHC n F2n+1-, CH2=CHC n F2n+1O-, CH2=CHC n F2n+1S-, R2OC n F2n+1-, R2OC n F2n+1O-, R2OC n F2n+1S-, CF3CH2-, CF3CH2O-, (CF3)2CH-, (CF3)2CHO-, CHF2-, CHF2O-, CHF2S-, CClF2-, CClF2O-, CClF2S-, , CClF2-, CCl2FO-, CClF2S-, CCl3,-CCl3O-, C6F5-, CF3C6F4-, C6F5O-, CF3C6F4O-, 3,5-(CF3)2C6H2-, C6Cl5-, C6Cl5O-, FSO2CF2-, ClSO2(CF2)n-, -SO3(CF2)n-, -SO3(CF2)n-, -CO2(CF2)n-, -SO3(CF2)n-, -2O3P(CF2)n-, FSO2N(-)SO2(CF2)n-, CF3SO2N(-)SO2(CF2)n-, C n F2n+1SO2N(-)SO2(CF2)n-, R1SO2N(-)SO2(CF2)n-, FSO2(CF2)n-, ClSO2(CF2)n-, -SO3(CF2)n-, -SO3(CF2)n-, -CO2(CF2)n-, -SO3(CF2)n-, C n F2n+1SO2N(-)(CF2)n-, R1SO2N(-)(CF2)n- where R2 has a similar definition than R, and 2 <= n <= 12.
3) Compound according to claim 1 characterised in that R is an alkyl, alkenyl, an aryl-alkyl, an aryl-alkenyl, an alkyl-aryl, an aryl-alkenyl, an alkyl-heterocyclic, heterocyclic-alkyl, from 1 to 28 carbon atoms, possibly including catenary heteroatoms in the for of ~O~, =N~, ~S~, =P~, =(P=O)~, ~SO~, ~SO2~ possibly bearing various functionalities
4) Compound according to claim 3 characterised in that the various functionalities include negative or positive ion-bearing groups, hydroxy, amine, solvating or complexing capabilities, double bonds and polymerization-active functionalities.
5) Compound according to claim 3 characterized in that R is chosen from C p H2p+1~, C6H5~, C6H5C p H2p~, C p H2p+1C6H4~, C p H2p+1C6H4C r H2r~, CH2=CHC p H2p~, CH2=CHC6H5~, CH2=CHC6H4C p H2p+1~, CH2=CHC p H2p C6H4~, , HOC p H2p~, (HO)CH2CH(OH)C p H2p~, HO[C2H4O]q C r H2r~, C p H2p+1O
[C2H4O]q C r H2r~(HO)CH2C2H4OC2H4~, HOC6H5~, HOCH2C6H5~, HOC p H2p+1C6H4~, HOC6H4C p H2p+1~, HO C p H2p C6H4 C p H2p~, CH2=CHC(=O)OC p H2p~, CH2=CHC(=O)OC6H4~, CH2=CHC(=O)OC6H4~, CH2=CHC(=O)OC p H2p C6H4~, CH2=CHC(=O)OC p H2p C6H4 C r H2r~, CH2=C(CH3)C(=O)OC p H2p~, CH2=C(CH3)C(=O)OC6H4~, CH2=C(CH3)C(=O)OC p H2p C6H4~, CH2=C(CH3)C(=O)OC p H2p C6H4C r H2r~, -O2CC p H2p~, -O2CC6H4~, [-O2C]2C6H3~, [-O2C]3C6H3~, -O2C C p H2p C6H4~, -O2CC p H2p C6H4C r H2~, -O3SC p H2p~, -O3S C6H4~, [-O3S]2C6H3~, [-O3S]3C6H3~, -O3SC p H2p C6H4~, -O3S C p H2p C6H4C r H2r~, -2O3PC p H2p~, -2O3PC6H4~, [-2O3P]2C6H3~, [-2O3P]3C6H3~, -2O3PC p H2p C6H4~, -2O3PC p H2p C6H4C r H2r, CF3SO2N(-)O2SC p H2p~, CF3SO2N(-)O2SC6H4~, [CF3SO2N(-)O2S]2C6H3~, [CF3SO2N(-)O2S]3C6H3~, CF3SO2N(-)O2SC p H2p C6H4~, CF3SO2N(-)O2SC p H2p C6H4C r H2r~, N.ident.CN(-)O2SC p H2p~, N.ident.CN(-)O2SC6H4~, [N.ident.CN(-)O2S]2C6H3~, [N.ident.CN(-)N(-)O2S]3C6H3~, N.ident.CN(-)O2SC p H2p C6H4~, N.ident.CN(-)O2SC p H2p C6H4C r H2r~, (N.ident.C)2C(-)O2SC p H2p~, (N.ident.C)2C(-)O2SC6H4~, [(N.ident.C)2C(-)N(-)O2SC2C6H3~, [(N.ident.C)2C(-)N(-)O2S]3C6H3~, (N.ident.C)2C(-)N(-)O2SC p H2p C6H4~, (N.ident.C)2C(-)N(-)O2SC p H2p C6H4C r H2r~, [C s H2s+1]3(+)NC p H2P~, ([C s H2s+1]3(+)NC6H4~,[C s H2s+1]3(+)NC6H3~, {[C s H2s+1]3(+)N}3C6H3~, [C s H2s+1]3(+)C p H2p C6H4~, [C s H2s+1]3(+)NC p H2p C6H4C r H2r~, [C s H2s+1]3(+)NC p H2p~, ([C s H2s+1]3(+)PC6H4~,[C s H2s+1]3(+)~PC6H3~,{[C s H2s+1]3(+)P}3C6H3~, [C s H2s+1]3(+)PC p H2p C6H4~, [C s H2s+1]3(+)PC p H2p C6H4C r H2r~, ([C s H2S+1]2(+)SC6H4~,[C s H2s+1]2(+)SC6H3~, {[C s H2s+1]2(+)S}3C6H3~, [C s H2s+1]2(+)SC p H2p C6H4~,[C s H2s+1]2(+)SC p H2p C6H4C r H2r~, C s H2s+n(+)[NC4H4]~, C s H2s+1(+)[NC3H3N]C p H2p~, [C s H2s+1O]3Si Cp H2p~, [C s H2s+1O]2Si(CH3) C
p H2p~
Where: (1<n, p<=48), (0 <=s<=18)
6) Compound according to claim 1 characterised in that is formed form two moieties A~B, either A or B, alternatively A and B being chosen from:

7) Polymer or co-polymers characterised in that they are prepared from the polymerisation or copylmerisation of compounds according to claim 1 containing active functionalities in R, R' of R F
8) Polymers or co-polymers characterised in that it comprises the repeat units:
where Q is a divalent organic radical containing between 1 and 240 carbon atoms and possibly including catenary heteroatoms in the for of -O-, =N-, -S-, =P-, =(P=O) -, -SO-, -SO2-
9) Polymer or co-polymers characterised in that it comprises the repeat units:

where represents a divalent organic radical containing between 1 and 240 carbon atoms and possibly including catenary heteroatoms in the for of -O-, =N-, -S-, =P-, =(P=O) -, -SO-, -SO2-.
10) Compounds according to claim 1 to 9 characterised in that the azino-bis-thiazoline units can form a radical cation and possibly a radical di-cation.
11) Compounds according to claim 10 characterised in that the radical canon is stable to air and to water.
12) Compound according to claim 1, as discrete molecule or under polymeric form characterised in that it is used as a redox mediator.
13) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used as an assay for laccases.
14) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used as redox shuttle for lithium batteries, either with liquid electrolytes or with polymeric electrolytes.
15) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used as active component for electrochromic windows.
16) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used a mediator for redox fuel cells on the positive electrode side.
17) Compound according to claim 1 as discrete molecule or under polymeric form characterised in that it is used a mediator for bleaching paper pulp and fibers with oxygen.
CA 2448618 2003-09-11 2003-09-11 New 2,2'-azino-bis-thiazolines as precursors to air-stable radicals Abandoned CA2448618A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA 2448618 CA2448618A1 (en) 2003-09-11 2003-09-11 New 2,2'-azino-bis-thiazolines as precursors to air-stable radicals
PCT/FR2004/002320 WO2005026136A2 (en) 2003-09-11 2004-09-13 2, 2'-azino-bis-thiazolines and uses thereof as air- and water- stable radical precursors

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